Special Situations (and Why I Sometimes Break My Own Rules)
By Sean McLaughlin
August 6, 2025
For the most part, I have a process.
I source ideas from my usual places. I scan for my favorite setups. I assess where implied volatility sits to inform what type of options strategy might have an edge. I figure out how much I’m willing to risk and define where the market would prove me wrong. Then I size the trade and map out potential profit targets.
That’s the rhythm. That’s the structure. And more often than not, it works.
But here’s the thing: when you stick to a process too tightly, it can start to feel…
Rote. Boring, even.
And when things feel boring, I find that laziness and sloppiness creep in. That’s when I know it’s time to wake myself up.
One way I do that is by paying attention to special situations—opportunities that don’t quite fit inside my normal framework, but that catch my eye anyway.
Take $UNH, for example:
United Healthcare, the largest healthcare provider in the country, has been under pressure lately. I’m not a long-term investor (I wish I were better at it), but I can’t help thinking this could be an interesting opportunity for someone with patience and solid risk management skills.
And then—just yesterday—JC calls me out of the blue and says: “Hey, I want to talk about $UNH.” Great minds, right? I’ll let him tell the story in full—you can read it here. It’s worth your time.
Now I’m thinking about putting a trade on. It’s not in my comfort zone. I don’t usually venture into “value investing” territory. But sometimes, the setup is just too compelling to ignore. And truthfully? I kind of like stepping out of bounds every now and then. Stretching into new trade types forces me to engage more deeply. It makes me pay attention. It helps me grow.
That’s the real opportunity.
And I think that’s worth something.
Sean McLaughlin | Chief Options Strategist, All Star Charts
